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If you use Windows a bit more you will learn to hate it with every fibre in your being!

Roaming profiles seems such a good idea, we use to have them at work, but IT found that with NT5 (2K) and particularly NT5.1 (XP) were so unreliable that they gave up on the idea, and roaming profiles are gradually being withdrawn.

The lack of a sane file system is also a pain. I understand that since NT5/2K you can mount drives or devices(?) within a unified path structure, but I've never seen an NT admin do this, they seem to prefer a profusion of drive letters. This means that if you use different machines you come un-stuck if you expect your paths to remain constant.

If I were you I'd hack a DOS batch script to start Bash from Cygwin. Once Bash has started it only uses it's own local and mostly sane file system, which shouldn't be dependent on the underlying broken Windows one. With Cygwin you get gcc, Perl and OpenSSH, all nice tools that work almost as if they were on a real computer. Nothing is perfect but if you stay within your Cygwin world on the NT system, things are pretty much okay.

To make Cygwin/Bash work like this, you have to fiddle with some DOS environment variables, and tamper with the PATH if I recall. Then you can run Bash as a login shell off the USB device, and Bash should behave the way you expect. You should also be able to get any SSH keys to behave the way you'd expect if you ssh-add them.

Windows isn't such a bad single user, non-networked GUI. It's just a shame that Microsoft put more emphasis in eye-candy than in making it work in a multi-user and networked environment.

Good luck with your struggles, as I'm forced to use Windows at work, I shall feel your pain every work day....